Top Movies with Men Playing Women or Vice Versa on Screen

From hilarious comedies to poignant dramas, Hollywood has a rich tradition of swapping scripts and letting men play women and women play men literally. And let’s be real—it’s always a wild ride.

Here are some of the most iconic (and unexpected!) gender-bending performances on the big screen:

1. Tootsie (1982) – Dustin Hoffman as Dorothy Michaels

Let’s start with the classic. In Tootsie, struggling actor Michael (Dustin Hoffman) lands a breakout role… as a woman. The film hilariously explores gender politics while showcasing Hoffman’s incredible transformation into Dorothy. It’s funny, heartfelt, and way ahead of its time.

2. Mrs. Doubtfire (1993) – Robin Williams as Euphegenia Doubtfire

One word: Legendary. Robin Williams disguised himself as a sweet British nanny to spend more time with his kids after a divorce—and it became one of the most beloved comedies ever. The voice, the wig, the prosthetics—pure gold.

3. White Chicks (2004) – Shawn and Marlon Wayans as Brittany and Tiffany

This one’s outrageous—in the best way. Two Black FBI agents go undercover as white socialite sisters, complete with blonde wigs, designer fits, and absurd Valley Girl accents. Campy? Absolutely. But it’s become a total cult classic.

4. She’s the Man (2006) – Amanda Bynes as Sebastian

Inspired by Shakespeare’s Twelfth Night, Amanda Bynes nailed the boy-next-door energy as she impersonated her twin brother to play on the boys’ soccer team. Add Channing Tatum and teen angst, and you’ve got one of the best gender-swap rom-coms.

5. Hairspray (2007) – John Travolta as Edna Turnblad

In true musical theatre tradition, Edna is often played by a man—and Travolta brought his A-game (and a whole lot of padding) to the motherly role in Hairspray. He sang, danced, and embraced the glam like a pro.

6. Victor/Victoria (1982) – Julie Andrews as a Woman Pretending to Be a Man Pretending to Be a Woman

Yes, it’s as complex as it sounds—and brilliant. Julie Andrews plays a struggling singer who finds success as a male female impersonator. Confused? Don’t worry, it all comes together in the most fabulous, jazzy way.

7. Cloud Atlas (2012) – Multiple Actors in Cross-Gender Roles

This ambitious sci-fi epic featured actors playing different roles across timelines—including gender-bending performances. Hugo Weaving as Nurse Noakes? Chilling. The Wachowskis didn’t hold back, and neither did the cast.

8. Albert Nobbs (2011) – Glenn Close as a Man

In this deeply emotional role, Glenn Close plays a woman who has lived as a man for decades in 19th-century Ireland to work as a butler. It’s a quiet, powerful performance that earned her an Oscar nomination.

9. The Danish Girl (2015) – Eddie Redmayne as Lili Elbe

While not a comedy, this film is a significant portrayal of one of the first known recipients of gender confirmation surgery. Redmayne played Lili Elbe with vulnerability and grace, sparking conversation and praise (alongside some controversy).

These roles go beyond just wigs and wardrobe changes—they explore identity, challenge norms, and open up conversations about gender and performance. Some made us laugh, others made us cry, but all of them left a mark.

Whether it’s drag, disguise, or deep identity exploration, Hollywood’s history of literal gender-bending roles is as fascinating as it is fabulous.